Last week I decided to reach out to some big investors and tell them about my startup, PenPath. My goal was to simply just be on their radar and hopefully get some feedback. One of the emails I sent was to Mark Cuban — a very famous entrepreneur I really look up to. Unfortunately, I didn’t have any mutual contacts or context to put me in touch, but decided to reach out anyways. Getting a reply the next morning with the name “Mark Cuban” in my inbox was surreal. I had quite a few people ask what he said and others wonder how I got him to even reply after I wrote a Facebook status about it, so I decided to write this and share some tips I used while drafting the email I sent him.

Note that Mark Cuban doesn’t need money so his time is pretty valuable and limited — which makes sense. It’s not like we had a big conversation either, but now he knows who I am and it could lead to more opportunities. I remember him saying in an interview that he reads all his emails, but if you don’t get a reply, you should get the hint. So I made sure to carefully craft an email before pushing send. I spent a long time on it too– read it over countless times, revising and changing things. This doesn’t necessarily mean I did everything right, nor do I think I’m an expert on this topic by any means. These tips simply ended up working for me, and have done so in the past. I’ve had successful replies that led to me meeting other idols such as Gary Vaynerchuck or Randy Komisar from Kleiner Perkins. Figured I’d share some tips I use with you and hopefully help out.

So things are going really well for my startup so far, and I’d like to know your thoughts.
I’ll give you a summary of my business, tell you about myself, and finally the current state of my startup. Thanks for reading! I know you’re very busy.

As I’m sure you know, the online publishing world is massive and keeps growing. There are almost 300mm blogs and 30mm bloggers online. Quality content is now essential for brands, publications, journalist and bloggers. You also have social media share buttons on every blog post displaying how well content is received by its readers. Social media has completely coated the internet and consumers are now aware that good content is fun to share with their friends — that’s why I think now is the perfect time to start my company. I know VC’s always asks their startups, “Why now?”

PenPath is a SaaS business platform that provides analytics to individual writers. Create your profile in minutes, and start tracking how engaged your readers are. PenPath helps writers measure their content’s influence through key metrics such as: social shares, SERP, comments, readability & more. Receive updates from all your work to know when it’s shared, liked, tweeted, pinned, commented, etc, no matter where it’s published, in one central location.

Having a profile also creates a social aspect to PenPath which lets writers follow each other, and would be a better way for the public to keep up with their favorite writer’s newest work. Popular writers contribute all over the web and the best solution to follow their work so far is with Twitter which is cluttered with all their other tweets.

Publishers, brands, and marketers can use PenPath’s data to find influential writers, track user engagement in real-time, and make better decisions since engaged users are much more likely to convert.

Other verticals include a database of ranked content people can search to find trending posts and this technology could also be used on an enterprise level.

This is a marketplace because the publications and brands need writers. We wouldn’t have the chicken or egg problem other marketplaces have because writers will be attracted to the analytics (freemium) and then the publications would follow. Publications could also use this software to track their current writers performance.

—- The rest of the email is about me and the story behind PenPath. —-

So I’m 23 years old, and I’m having the best time starting this business. I’ve been an entrepreneur all my life. While I was in college (Mizzou) I started a digital magazine for college students. I had it reach a few million people in two years during which I learned about building a successful internet brand. It was a top 100k website on Alexa, and had writers from all over the country — students from Mizzou, Harvard, OSU, Berkeley, UC Davis, and many more all contributed.

After college, I was hired by Northrop Grumman doing inbound marketing strategy. I’ve applied a lot of my knowledge in SEO, SEM, content marketing, and social media to help grow their laser division’s brand and online leads. I started with a $50K budget and since taking over, its led to nearly $1mm in sales.

Earlier this year, I was explaining to my friend how difficult finding and vetting good writers was when I realized there was no objective way to measure their performance.

As a publication, I had many tools to know how my site performs as a whole, but nothing to track individuals.

After two months of market research, surveys, and interviews, the feedback was overwhelmingly positive. I made a landing page listing all the possible features to see if people would even sign up to use it, and sure enough, people started to sign up — not just small time bloggers either. In a little over one month, I’ve had almost 150 people register including writers and publications. I know that’s not many, but it’s certainly a sign of life as Paul Graham would say. I even started to get emails from random people asking when the beta would be released.

I would like to work with you for obvious reasons. It’s not just about the money. I’m a designer and product focused founder. I’m %1000 committed and know the industry. I would love the opportunity to pitch to you in person, or whatever the next step may be.

I’ve attached some of my designs to this email, our prototype works great, and I have a good friend doing the development right now. You can see the prototype here: penpath.heroku.com

Our quality landing page here: PenPath.com

I apologize for the long email. Looking forward to hearing back from you!

So here are 5 Tips that I used to get Mark Cuban to reply to my email:

#1 Avoid Rookie Mistakes

Before you even worry about what you’re going to do right, ante up and make sure you don’t do anything wrong. If you are contacting someone like Mark, they don’t have time for people who don’t cover the essentials. Aside from avoiding trivial mistakes, there are various other things you should never do in a first email. Don’t ask anything a Google search could answer for you. Don’t go off topic or express opinions they probably won’t care about. Have people skills, but don’t try to be their friend yet. Don’t let the person you really want to respond be the first person you try to email. Try other local investors (in my situation) or business people in your community so you can get comfortable and gain email experience. You’ll be able to learn common etiquette and understand how this type of communication works in your industry. Use common sense — try asking people you know to read through it and give you feedback before sending it. You get the point — I’d bet avoiding simple mistakes will separate you from 90% of the random emails someone like Mark gets.

#2 Structure Your Thoughts

An email is an idea, and anytime you express an idea it’s not always what you say that matters, it’s how you say it. You have to deliver information and guide the reader through your thoughts clearly. A tip I give to people when structuring an email or content is to ALWAYS outline what you plan on saying first. What are the headlines of your idea and in what order would it be best to deliver them in. I use a technique I learned in speech class which is: when you start a speech (or communicate any idea), tell people what you are going to tell them, tell them what you came to tell them, and then tell them what you told them. I can’t stress how helpful that tip has been for me.

While editing the email I sent Mark, I changed the structure so it would have the meat of the content in the very beginning, before I even mentioned anything about me. I didn’t waste any time with fluff in the opening. So even though he’s basically one of the top 3 people I’d like to meet in this world, the most you see from me admiring him are like 6 words before jumping right into the pitch. So remember to be diligent and plan out your thoughts before even writing that email.

#3 Do Your Homework

Most times you won’t get an answer since they are so busy, so you might decide to slack when it comes to preparation. I’m telling you, if you are serious about getting a response or opening up a big opportunity for yourself, you have to do your homework. Know about the person, know what they like, know how they think, what they are up to before contacting them. Having an understanding of their personality can help you create an email that connects better with them. Unfortunately, people skills aren’t an exact science, but if you have access to videos or blog posts from them, you will get a much better feel for things. You’re already reading this but doing your homework also includes something as simple as a Google search on how to write a good email. One of the most helpful videos I’ve seen about email tips was from Rand Fishkin from Moz.com. You can read the article here: What Separates a “Good” Outreach Email from a “Great” One? – Whiteboard Friday

#4 Be Concise

How long do you make an email to someone who’s too busy? You still want to add all the important information, but what if it’s still too long? I had this problem. The solution that I used was to structure the email like I said on tip 2 so the most important info is in the beginning, but I also made sure to section off the supporting information in the second half of the email. I squeezed the business pitch into the beginning and then sectioned off the part where I tell him about me and the current state of PenPath. Other than that, you need to cut down the information to the essentials and hope they read it all. Also, don’t be too choppy. If it flows well (something I struggle with) they will hopefully be able to read through it quickly.

#5 Give Them Value

If you are emailing cold, you need to add some sort of value to them. So what do I mean by value? It could be anything. A sincere compliment about something they just did or are currently working on is valuable. Maybe the content you are emailing them is enjoyable to read — that technically is providing value in my book. Mark Cuban likes technology so a well written article about a tech startup might be interesting to him. Not saying mine was, but I tried to make it as interesting as I could. Another thing that may add value is if they have something to gain from helping you. If Mark decides to eventually work with me and invest, he would make money, so that’s more of a long term value option that could be of interest, but it could be something like your network or a specific contact that person could benefit from. Try adding a quick relevant mention about the “value” you offer. Again, when dealing with a Mark Cuban, you probably don’t have much to offer so stick to the first value ideas I suggested.

If you subscribe to my blog posts, I’ll send you the final tip that makes you do all this and save a LOT of time.I hope those tips helped. Remember that if the person you are trying to reach is busy and important, they might not respond. Don’t take it to heart and keep trying others. I had no contacts who knew Mark Cuban, but having a reference or mutual contact is ALWAYS the best way to get in touch with someone. With today’s connected world, if you want it bad enough, you can get it. I’m always learning and trying to refine my skills. I’d love to hear your thoughts on these tips. My question to you is:

What pet-peeves or advice do you have when it comes to emails? Leave your thoughts the comment section.

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Alex Cruz

Welcome to my blog! We are living through some of the most revolutionizing times in history as technology disrupts everything in its path and paves the way for new more efficient ways to take it's place. As a founder of a software startup (PenPath.com) and consultant for companies both big and small, I share my best nuggets of information with you though my blog. I hope it helps you out. For more about me, check out the about page.
-Alex